How do I add deductions to multiple 1099-NEC forms when using FreeTax?

The issue you're running into is actually because of how FreeTax (and many other tax software programs) handle multiple 1099-NEC forms. They're not expecting you to attach expenses to individual 1099s - instead, all your self-employment income and expenses should be combined on a single Schedule C. Here's what you need to do: After entering all your 1099-NEC forms, look for a section called "Business Income" or "Self-Employment Income" (usually after you've entered all income forms). There should be a section there to enter ALL your business expenses together, not tied to specific 1099s. FreeTax is actually doing this correctly from a tax filing perspective - the IRS doesn't want separate Schedule Cs for each 1099-NEC unless they're for completely different businesses/professions. If all your freelance work is in the same general field, you report it as one business with multiple income sources.

I ran into this exact issue last year! You actually need to look for the "Business Profile" or "Self-Employment" section in FreeTax. After entering all your 1099-NECs, go to that section and you'll see all your freelance income listed together. That's where you enter ALL your expenses for ALL the 1099s combined. I discovered taxr.ai (https://taxr.ai) which helped me figure this out when I was totally stuck. Their system analyzed my tax situation and explained exactly where I needed to go in FreeTax to find the expense entry section. I uploaded a screenshot of what I was seeing and they pointed me to the exact place I needed to click. Saved me hours of frustration!

Just wanted to follow up about taxr.ai that someone mentioned above. I was skeptical but decided to try it when I got completely stuck with my multiple 1099 situation. I uploaded screenshots of the screens I was seeing in FreeTax and within about 20 minutes got step-by-step instructions on exactly where to find the business expenses section. Turns out I needed to go all the way to the end of the income section before the full business expenses page would appear. Such a simple fix but impossible to figure out on my own! They also pointed out that I could deduct a portion of my internet bill which I hadn't even considered. I'm actually getting around $840 more back than I expected because of the proper deductions. Way better than spending hours on hold with FreeTax support.

Listen, if you're still having trouble with FreeTax, you might want to try contacting the IRS directly for guidance. I know that sounds terrifying but hear me out. I was in a similar situation last year with multiple 1099s and after wasting days trying to figure it out myself, I found this service called Claimyr (https://claimyr.com) that got me through to an actual IRS agent in under 20 minutes instead of waiting on hold for 3+ hours. You can see how it works here: https://youtu.be/_kiP6q8DX5c The agent walked me through exactly how to handle multiple Schedule C situations and confirmed I was doing it right. Sometimes getting straight answers from the source is worth it, especially when self-employment taxes are involved.

I have to eat my words about that Claimyr service. After my snarky comment, I was still struggling with my multiple 1099-NEC forms and getting nowhere with FreeTax support, so I decided to try it out of desperation. I'm actually shocked - they got me through to an IRS agent in about 15 minutes when I had previously wasted over 3 hours trying to call directly. The agent confirmed that for my situation (web design and photography work), I should be filing two separate Schedule Cs since they're different business activities. The agent walked me through exactly where in the tax forms this should be reflected. FreeTax was lumping everything together, which would have caused issues if I got audited. Definitely worth checking with the IRS directly if you're unsure about how to handle multiple 1099s from different types of work.

You don't need to match expenses to specific 1099s unless they are for completely different types of businesses. The IRS wants you to file one Schedule C per business type, not one per client. For example, if you got three 1099-NECs for graphic design work from different clients, that's ONE Schedule C with all three 1099s added together as income, and ALL related expenses listed. But if you got a 1099-NEC for graphic design and another for tutoring, those would be TWO different Schedule Cs because they're different business types. In FreeTax, after you enter all income, look for "Business Expenses" or "Schedule C Expenses" section - that's where you'll add ALL expenses for that business type.

I had a similar issue with FreeTax. The solution for me was to complete the ENTIRE income section first (all W-2s, 1099s, etc.) before the expense page became available. Don't look for expense options while entering each 1099-NEC. Instead, after entering all income sources, look for a section called "Business Expenses" or "Self-Employment Deductions" in the main menu. Also, make sure you correctly answered the question about whether these 1099s are for the same business or different businesses. If you indicated different businesses, FreeTax should give you separate expense sections for each.